PL6875B1 - The method of obtaining azo dyes. - Google Patents
The method of obtaining azo dyes. Download PDFInfo
- Publication number
- PL6875B1 PL6875B1 PL6875A PL687526A PL6875B1 PL 6875 B1 PL6875 B1 PL 6875B1 PL 6875 A PL6875 A PL 6875A PL 687526 A PL687526 A PL 687526A PL 6875 B1 PL6875 B1 PL 6875B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- azo dyes
- amino
- obtaining azo
- naphthol
- Prior art date
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- 239000000987 azo dye Substances 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 9
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010017 direct printing Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Description
Wykryto, iz sprzegajac w srodowisku alkalicznem i kolejnosci dowolnej zwiazki czteroazowe 2, 2'-dwuhalogeno- wzglednie 2, 2 dwualkylo- /,4'-dwuaminodwufenylu z jedna czastka molowa kwasu fenylodwu- aminodwusulfonowego, jako to kwasu 1,3- fenylenodwuaminodwusulfonowego i jedna czasteczka molowa kwasu 2-amino-8-naf- tolo-6-sulfonowego lub jego pochodnych, podstawionych w grupie aminowej, otrzy¬ muje sie nowe cenne barwniki azowe.Barwniki te daja na welnie w kapieli kwasnej odporne na zcieranie wybarwie- nia czerwono-brunatne. Szczególnie nadaja sie one, dzieki swej rozpuszczalnosci, do bezposredniego druku na welnie i jedwa¬ biu, dajac pelne odcienie czewono-bru- natne o bardzo dobrej odpornosci na dzia¬ lanie wody.Przyklad. 253 czesci wagowych 2,2'- dwuchloro-4,4'-dwuaminodwu fenylu dwu- azuje sie jak zwykle 138 cz. wag. azotynu sodowego i niezbedna iloscia kwasu solne¬ go. Roztwór zwiazku czteroazowego wle¬ wa sie do chlodnego, zakwaszonego kwa¬ sem octowym roztworu 268 cz, wag. kwa¬ su 7,3-fenylenodwuamino-4,6-dwusulfono- wego.Sprzeganie dobiega do konca po uplywie okolo */2 godziny i wytraca sie produkt posredni. Utrzymujac nadal roztwór w temperaturze niskiej, alkalizuje sie go so-da i dodaje natychmiast roztwór 239 cz. wag, kwasu 2-amino-8-naftolo-6-sulfono- wego w nadmiarze sody. Po ukonczonem sprzeganiu barwnik wysolony tworzy su¬ chy ciemno-brunatny proszek, rozpuszcza¬ jacy sie w wodzie z zabarwieniem czerwo- no-brunatnem, w kwasie zas siarkowym — z zabarwieniem niebiesko-czerwonem.Przy drukowaniu bezposredniem na welnie i jedwabiu otrzymuje sie pelne czerwono-brunatue odcienie, bardzo od¬ porne na dzialanie wody.Barwnik otrzymany w sposób podobny z 2,2'-dwumetylo-4,rf'-dwuaminodwufenylu (m-toluidyny) posiada zupelnie takie same wlasnosci.Stosujac akylo- i arylo podstawione produkty kwasu 2-amino-8-naftolo-6-sulfo- nowego otrzymuje sie odcienie bardziej zólte. PL PLIt has been found that, in an alkaline and sequential bonding of any compound, 2, 2'-dihalo or 2, 2 dialkyl /, 4'-diaminodiphenyl with one mole particle of phenyldiaminodisulfonic acid, as is 1,3-phenylenediamine disulfonic acid and one disulfonic acid The molar molecule of 2-amino-8-naphthol-6-sulfonic acid or its derivatives, substituted in the amino group, gives new valuable azo dyes. These dyes give on the wool in the acid bath abrasion-resistant reddish-red dyes. brown. Due to their solubility, they are particularly suitable for direct printing on wool and silk, giving full shades of reddish brown with very good water resistance. Example. 253 parts by weight of 2,2'-dichloro-4,4'-diamino phenyl are diazotized as usual with 138 parts. wt. sodium nitrite and the necessary amount of hydrochloric acid. The solution of the four-phase compound is poured into a cool, acetic acid-acidified solution of 268 parts by weight. 7,3-phenylenediamine-4,6-disulfonic acid. The heating is complete after about 1/2 hour and the intermediate product is precipitated. Keeping the solution still at a low temperature, it is made alkaline with sodium and immediately added a solution of 239 parts. by wt, 2-amino-8-naphthol-6-sulfonic acid in an excess of sodium. After the coupling is completed, the salted dye forms a dry dark-brown powder, which dissolves in water with a red-brown color, in sulfuric acid - with a blue-red coloring. Direct printing on wool and silk gives a full red color. - brown shades, very resistant to water. The dye obtained in a similar manner from 2,2'-dimethyl-4, rf'-diaminodiphenyl (m-toluidine) has exactly the same properties. Using acyl- and aryl-substituted acid products 2-amino-8-naphthol-6-sulfonic acid gives more yellow shades. PL PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL6875B1 true PL6875B1 (en) | 1927-03-31 |
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